Recently, an increasing number of sinkholes related to cavernous karst bedrock has been documented in the Kingdom of Saudi Arabia (KSA). One of the most hazardous areas is Al Jouf region, with an average annual rainfall below 35 mm. Here, crop fields irrigated with groundwater have experienced a very rapid expansion. Limited hydrogeological data indicate that the over-exploitation of the aquifers with very low recharge have caused a decline of around 50 m in the groundwater level. Landsat images acquired in 2002, 2015, and 2018 were utilized to automatically map and assess the expansion of agricultural activities in the area, as a proxy for groundwater withdrawal. The data indicate a rising expansion rate, from 57 km2/yr in the period 2002–2015, to 123 km2/yr during the 2015–2018 interval. The recent sinkhole spate is attributed to the growth of irrigated crops and the associated groundwater level decline, as supports the temporal and spatial correlation. It is proposed that the water level drawdown entails an increase in the effective weight of the roof of relict cavities formed in the past. This interpretation is substantiated at a specific sinkhole investigated by ERT. The geophysical investigation provides information of the position of the underlying cavity and indicates that its roof has been affected by buoyancy loss related to the anthropogenic water level decline.